Molly is so focused on directing a school recital that she doesn't realize a fellow teacher is hitting on her. Meanwhile, Vince convinces Mike to join him in an unusual money-making scheme.
Mike goes on a junk food binge to cope with missing Molly while she is out of town for a teacher's conference. Meanwhile, Carl contemplates leaving Chicago after learning heartbreaking news from James.
After learning that Joyce gave up her artistic talents when she became a mother, Molly decides that she and Mike need to pursue new hobbies before becoming parents, so they take up roller skating.
Mike's birthday wish is to have his wife and mother get along, but Molly and Peggy butt heads more than ever as they try to plan his birthday party together. Meanwhile, Samuel and Carl compete for the same woman.
Molly joins her sister on a spring break road trip to party with Victoria's friends from junior college. Meanwhile, Mike pulls strings with his boss to get special overtime assignments in hopes of making extra money.
Mike decides to take things into his own hands and find out if he is fertile enough to make a baby with Molly. Meanwhile, Vince starts working as a door-to-door vacuum cleaner salesman.
Harry decides to ask Victoria out on a date for Valentine's Day, and she surprisingly accepts. Meanwhile, Carl and Samuel try to pick up women at the laundromat.
Mike starts construction on the basement in the Flynn house, but it turns out to be a more of a challenge than he thought. Meanwhile, Samuel becomes Carl's new roommate.
Mike is frustrated when Molly's Christmas spirit takes over and starts spending a lot of money. Meanwhile, Victoria new karaoke machine is the main attraction at the Flynn home, and Peggy forces Mike and Molly to spend Christmas Eve with her and the Captain at church.
Molly couldn't be happier that she doesn't have to cook Thanksgiving dinner when Mike gets sick. But when Vince asks his brother to join them for dinner Molly pitches in. Being engaged for a year, Joyce decides to press Vince marriage. Carl takes Samuel with him to the Thanksgiving dinner at his church with the expectation of meeting some young women.
When she realizes that her house is becoming too crowded, Molly decides to have a yard sale. Meanwhile, Mike and his friends take Carl for a fishing trip to help him get over his recent breakup.
Joyce bails when Vince throws out his back, forcing Mike and Molly to take care of him. Meanwhile, the newlyweds also have trouble writing personalized thank-you notes for their wedding gifts.
Mike and Molly prepare to return home from their honeymoon, and Mike seems to be a changed man. Meanwhile, Carl is frustrated by not hearing from Mike, and Molly's family spend their last moments getting drunk before the newlyweds return home.